Disinfectant compositions



United States Patent 2,874,087 DISINFECTANT COMPOSITIONS Albert JakobObladen, Hamburg-Gross Flottbek, and

Martin Karl Deutsch, Hamburg-Wandsbek, Germany No Drawing. ApplicationFebruary 17, 1956 Serial No. 566,095

This invention relates to disinfectant or antiseptic compositions. Moreparticularly it relates to antiseptic compositions containing mixturesof bactericidal phenolic compounds and polyhalogenated phenolates.

Many phenolic compounds, that is aromatic compounds having a freehydroxyl group directly attached to the nucleus are known to possessgermicidal properties of varying degrees of efficacy. Polyhalogenatedphenols, such as pentachlorophenol, are also known to possess antisepticproperties see, for instance, U. S. Patent No. 2,698,301, dated December26, 1954). In German Patent No. 649,172 mixtures comprising certainphenolic derivatives are described as having a synergistic bactericidaleffect. It is well known, however, that phenolic compounds lose theirantiseptic power in alkaline media. According to'the aforesaid U. S.Patent No. 2,698,301 effective antiseptic detergent compositions can beprepared from detergent soaps and 0.5 to 5% by weight of apentahalogenated phenol, such compositions being stated to be effectiveagainst Staphylococci. The pentahalogenated phenols are, however,substantially insoluble in water and to incorporate them in a detergentsuch as soap or an alkyl sulphonate, the pentahalogenated phenol isfirst dissolved in a suitable solvent. The Water-solubility of thealkali metal phenolates increases with the alkali content but thegermicidal activity thereof decreases correspondingly with the increasedalkali content (see, for instance, E. Hailer in Weyls HandbuchderHygiene, 1922, vol. 8, page 1113). This decrease in germicidal powerwith increase in alkali content is true not only for monochlorinatedphenols but also for polychlorophenols.

It is an object of the present invention to provide novel disinfectantor antiseptic compositions which comprise V polyhalogenated phenols inwater-soluble or readily dispersible form, that is in the form ofwater-soluble phenolates such as the alkali metal phenolates, suchcompositions having a high bactericidal or antiseptic power.

It has now been discovered that the polyhalogenated phenolates,especially potassium or sodium pentachlorophenolates, considerablyincrease the germicidal activity of bactericidally-active phenoliccompounds in general, rather than decrease it as was to be expected andhence this surprising result permits aqueous, disinfectant solutions ofphenolic compounds of high potency to be prepared.

In accordance with this invention disinfectant compositions are formedof mixtures of bactericidal phenols, including phenolic derivatives, andsalts of polyhalogenated phenols with inorganic or organic bases,especially pentachlorophenolates, such as sodium or potassiumpentachlorophenolates. The preferred disinfectant compositions of thisinvention comprise aqueous solutions of the phenolic mixtures andpreferably include a surface-active agent, such as a soap or detergent,for example, a higher alkyl or aryl-alkyl sulphonate. Particularlyeffective disinfectant compositions of this invention comprise a mixtureor two or more bactericidal phenols or phenolic compounds and apolyhalogenated phenolate, such as an ice alkali metalpentachlorophenolnte or pentabromophenolate. Thus effective disinfectantcompositions may com prise mixtures of parachlorometacresol and alsophenyl phenol in suitable relative proportions and conveniently insubstantially equal proportions. Such a mixture of bactericidal phenolsmay then be mixed with suitable proportions of a polyhalogenatedphenolate, the proportion of polyhalogenated phenolate varying fromabout 10% by weight of the bactericidal phenol or mixture of phenols to200% by Weight thereof or even more. However, it is economicallyconvenient and effective as an antiseptic for the composition to containone part of polyhalogenated phenolate per each 0.5 to 1.5 parts ofbactericidal phenol, for example, substantially equal proportions ofphenolates to bactericidal phenol or mixture theroef is a convenient andeffective relative proportion.

The proportion of surface-active agent such as soap may be andpreferably is a multiple of the proportion of bactericidal phenol in themixture. Suitable proportions of soap may, however, vary from 5% byweight to 500% by weight of the bactericidal phenol in the composition.In a satisfactory disinfectant composition in accordance with thisinvention the proportion of soap or other surfaceactive agent is equalto 1.5 times the weight of bactericidal phenol in the mixture.

The composition preferably includes substantial amounts of water and inits preferred concentrated form it is a liquid composition in which thetotal dissolved solids amount to 5% to by weight, the balance beingwater, a preferred range of total solids amounting to 30 to 75% byweight of the total mixture. Such solutions may be diluted many times toform effective disinfectants. The compositions of this invention mayalso include alkali such as sodium or potassium hydroxide or otherwater-soluble base, in amounts not in excess of the chemicallyequivalent proportion to convert the bactericidal phenols intophenolates, and preferably substantially less than the equivalentproportion, for example, about half the equivalent amount.

In the following examples, which are illustrative of this inventionsolutions are prepared of mixtures -of bactericidal phenols with andwithout the inclusion of pentahalogenated phenolates, and the antisepticpower of the different solutions, when diluted, is compared in thesubsequent tabulation. In the examples the parts are by weight. The soapused in Examples 1, 2 and 5 was prepared by saponifying castor oil with4.4% by weight of potassium hydroxide in the presence of 10%methylglycol.

Example I 6 parts para-chloro-meta-cresol, 6 parts ortho-phenylphenol, 118 parts soap,

made up to parts with water.

Example 2 6 parts para-chloro-meta-cresol,

6 parts phenylphenol,

18 parts soap,

10 parts potassium pentachlorophenolate, made up to 100 parts withwater.

This mixture therefore differs from solution of Example 1 because of itspotassium pentachlorophenolate content.

Example 3 5 parts parachlorometacresol,

5 parts orthophenylphenol,

1.7 parts sodium hydroxide,

50 parts of a fatty alcohol sodium sulphonate, 6 parts methylglycol,

made up to 100 parts with water.

Example 4 5 parts parachlorometacresol, 5 parts orthophenylphenol,

- 1.7 partssodium hydroxide,

50 parts fatty alkyl sodium sulphonate, parts sodiumpentachlorophenolate, made up to 100 parts with water.

This preparation differs from Example 3 because of its sodiumpentachlorophenolate content.

Example 5 For comparison a solution was used consisting of 18 partssoap, 10 parts sodium pentachlorophenolate, made up to 100 parts withwater.

Solution N o. Staph. aureus B. coli The tests clearly show that theaddition of potassium pentachlorophenolate or the corresponding sodiumsalt to the disinfectant solutions Nos. 1 and 3, which according totheir compositiom'are important in the trade as fine and coarsedisinfectants (Ullmann, 3rd edition, vol. 5, page 760), causes a verysignificant increase in the chiciency of the phenol mixtures (containingfree hydroxyl) which condition the disinfecting action,'although it isshown by the test with preparation 5 that sodium pentachlorophenolateper se is practically without effect in the same proportion. A reductionof the limiting killing concentrations of preparations 2 and 4 by avalue of 10. each, calculated on the species of germs Staph. aureus andB. c 0 li might have beenexpecte'd. .However, a 100% increase in degreeof efiiciency of the disinfectant is obtained, as seen particularlybycomparing preparations 3 and 4.

As germicidal or bactericidal phenols having free hydroxyl groups, thosewhich are known to be satisfactory in the art of disinfecting aresuitable for inclusion in the compositions of this invention, name,phenols, chlorophenols, chlorocresols, xylenols, chloroxylenols,phenylphenol, chlorophenylphenol, cyclohexylphenol,ehlorocyclohexylphenol, benzylphenol, chlorobenzylphenol,dihydroxydiphenylmethanes, dihydroxy diphenylsulphides anddihydroxydiphenyl-oxides, and their cloro derivatives, resorcinol andits derivatives such as hexylresorcinol etc.

Suitable polychlorophenolates for inclusion in the compositions for thisinvention are the salts of polychlorophenols with alkali metals,ammonia, amines or other organic bases such as the salts of -tri-,tetraand pentachloroor -bromo-phenols, triand vtetra-'chlorocresol,tetrachloroxylenol, tetrachloronaphthol and the like. The compounds ofhigher degree of chlorination show greater germicidal capacity than dothe lower.

The disinfectans prepared according to the invention have inpractice'the same technical properties as have well known fine andcoarse disinfectans of the kinds characterized by the examples. Thesolutions have good foaming properties, they are non-irritant to theskin etc. and have only a faint inherent odor and are versatile in use.

In the biological action'the new preparations resemble those which havebeen used hitherto, except that a considerable increase in efliciencyrelative thereto is obtained. Infection excitersof' all known kinds aredestroyed with a short time and under the use of economicconcentrations.

A meritorious feature of the invention resides in the possibility toachieve biological effects which go quite considerably beyond thoseknown hitherto and in some cases result in an improvement in the knowneffect up to even as much as twice the original figure.

We claim:

1. A disinfectant composition comprising 5% to 6% ofpara-chloro-meta-cresol, 5% to 6% "ortho-phenylphenol, 10% alkalimetalpentachloro-phenolate and the balance of a surface-active agent andwater.

2. The disinfectant composition of claim 1 which comprises 10% potassiumpentachl'oro-ph'enolate, and 18% soap.

3. The disinfectant composition of claim 1 which comprises 10% sodiumpentachloro-phenolate, '1.'7 %"so'dium hydroxide and of a higheralkylsulphonate.

4. A disinfectant composition comprising from 5% to 25% by weight ofparachlorinated cresol and'phenyl phenol, from 5% to 25% by weight ofalkali metal polychlorinated phenolate, and the balance of a surfaceactive agentand water.

References Cited in the file of'this patent UNITED STATES PATENTS1,248,181 Sidwen Nov. 27, 1917 FOREIGN PATENTS 461,883 Canada Dec. 20,1949 OTHER REFERENCES Reddish: Antiseptics, Disinfectants, Fungicidesand Sterilization (1954), page 442.

1. A DISINFECTANT COMPOSITION COMPRISING 5% TO 6% OFPARA-CHLOARO-META-CRESOL. 5% TO L% ORTHO-PHENYLPHENOL, 10% ALKALI METALPARA-CHLORO-META-PHENOLATE AND THE BALANCE OF A SURFACE-ACTIVE AGENT ANDWATER.